74936-69-9

Basic information

• Product Name: 3,5-Pyridinedicarboxylicacid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, 3-(1-methylethyl) ester
• Synonyms: 3,5-Pyridinedicarboxylicacid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, mono(1-methylethyl) ester(9CI); BAY-m 4270
• CAS NO: 74936-69-9
• Molecular Formula: C18H20 N2 O6
• Molecular Weight: 360.367
• Mol File: 74936-69-9.mol
• Article Data: 11

Chemical Properties

• CAS DataBase Reference: 3,5-Pyridinedicarboxylicacid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, 3-(1-methylethyl) ester(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-Pyridinedicarboxylicacid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, 3-(1-methylethyl) ester(74936-69-9)
• EPA Substance Registry System: 3,5-Pyridinedicarboxylicacid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, 3-(1-methylethyl) ester(74936-69-9)

Safety Data

• Hazardous Substances Data: 74936-69-9(Hazardous Substances Data)

Upstream product

• 14205-46-0 isopropyl 3-aminocrotonate 
• 110-71-4 1,2-dimethoxyethane 
• 74936-70-2 3-(2-cyanoethyl) 5-isopropyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate 
• 39562-25-9 3-oxo-2-(3-nitrophenylmethylene)butanoic acid isopropyl ester 
• 118431-79-1 2-[(3-nitrophenyl)methylene]-3-oxobutanoic acid,1-methylethyl ester 
• 99-61-6 3-nitro-benzaldehyde 
• 542-08-5 isopropyl acetoacetate 
• 143093-33-8 isopropyl β-aminocrotonate 

Relevant articles and documents

Noncovalently Functionalized Commodity Polymers as Tailor-Made Additives for Stereoselective Crystallization

Stereoselective inhibition of the nucleation and crystal growth of one enantiomer aided by “tailor-made” polymeric additives is an efficient method to obtain enantiopure compounds. However, the conventional preparation of polymeric additives from chiral monomers are laborious and limited in structures, which impedes their rapid optimization and applicability. Herein, we report a “plug-and-play” strategy to facilitate synthesis by using commercially available achiral polymers as the platform to attach various chiral small molecules as the recognition side-chains through non-covalent interactions. A library of supramolecular polymers made up of two vinyl polymers and six small molecules were applied with seeds in the selective crystallization of seven racemates in different solvents. They showed good to excellent stereoselectivity in yielding crystals with high enantiomeric purities in conglomerates and racemic compound forming systems. This convenient, low-cost modular synthesis strategy of polymeric additives will allow for high-efficient, economical resolution of various racemates on different scales.

Syntheses, calcium channel antagonist and anticonvulsant activities of substituted 1,4-dihydro-3,5-pyridinedicarboxylates containing various 3-alkyl ester substituents

A group of 3-alkyl-5-isopropyl 4-aryl-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylates 10-20 containing an amine, quaternary ammonium, aryl(heteroaryl)alkenyl, 4-(4-fluorophenyl)-piperazin-1-yl or methoxy moiety in the C-3 alkyl ester R-substituent in combination with a C-4 phenyl ring bearing a 2,3-Cl2, 3-NO2, 3-NMe2, 4-NMe2 or 3,4,5-(OMe)3 X-substituent were prepared using the Hantzsch 1,4-dihydropyridine reaction. In vitro calcium channel antagonist activity (CCA) was determined using a guinea pig ileum longitudinal smooth muscle assay. In the C-4 3-nitrophenyl series of compounds, the C-3 ester R substituent was a determinant CCA activity where the relative potency order was -CH2CH2CH=C-(2-methylphenyl)2 ≤ -CH2CH2NMe2.HCl > -CH2CH2CH=C (3-methyl-2-thienyl)2 > -CH2CH2+NMe3I-. The position and nature of the C-4 phenyl X-substituent, were also determinants of CCA activity where the relative activity order was 3-NMe2>4-NMe2>3,4,5-(OMe)3. Anticonvulsant activities were determined in mice using the subcutaneous metrazol (scMet) and maximal electroshock (MES) screens. The compounds investigated were generally not effective for protecting against scMet induced seizures, except for 10 {X = 2,3-Cl2, R = 2-[4-(4-fluorophenyl)piperazin-1-yl]ethyl} and 14a (X = 3-NMe2.HCl, R = CH2CH2OMe), which exhibited modest activity. Compound 11a (X = 3-NO2, R = -CH2CH2NMe2.HCl) was the most effective agent in the MES screen. All of the compounds investigated, except for 11b (X = 3-NO2, R = -CH2CH2+NMe3 I-, Kp = 0.15) are lipophilic with n-octanol/aqueous phosphate buffer (pH = 7.4) partition coefficients (Kp) in the 121-424 range relative to the reference drug nimodipine (Kp = 187). The structure-activity relationship acquired reinforce the concept that calcium is only one of several factors that are involved in seizure generation.

Process for preparation of enantiomerically pure polysubstituted 1,4-dihydropyridines

A process for the optical resolution of racemic 1,4-dihydropyridines, containing isothioureido groups. Salification of racemic isothioureas with optically active acids produces diasteroisomeric mixtures of isothiouronium salts, that, using conventional techniques, are separated in the individual components to give optically pure isothioureides of 1,4-dihydropyridines and salts thereof with conventional acids. Said optically pure 1,4-dihydropyridines can then be subjected to desulphuration and to different transformations to give to other enantiomerically pure and therapeutically useful 1,4-dihydropyridines.